Abstract
The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.
| Original language | English |
|---|---|
| Pages (from-to) | 2348-2355 |
| Number of pages | 8 |
| Journal | Crystal Growth and Design |
| Volume | 5 |
| Issue number | 6 |
| DOIs | |
| State | Published - Nov 1 2005 |
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ASJC Scopus subject areas
- Chemistry(all)
- Materials Science(all)
- Condensed Matter Physics
Cite this
Viability of a covalent chiral auxiliary method to induce asymmetric induction in solid-state photoreactions explored. / Natarajan, Arunkumar; Mague, Joel T.; Ramamurthy, Vaidhyanathan.
In: Crystal Growth and Design, Vol. 5, No. 6, 01.11.2005, p. 2348-2355.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Viability of a covalent chiral auxiliary method to induce asymmetric induction in solid-state photoreactions explored
AU - Natarajan, Arunkumar
AU - Mague, Joel T.
AU - Ramamurthy, Vaidhyanathan
PY - 2005/11/1
Y1 - 2005/11/1
N2 - The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.
AB - The effectiveness of covalent chiral auxiliaries in inducing stereoselectivity during the Yang type II photocyclization reaction was examined using the benzonorbornene phenyl ketone (2) and α-adamantylacetophenone (7) systems. The outstanding ability of covalent chiral auxiliaries in generating high asymmetric induction in the photoproducts has been established in 7 of the 10 investigated examples. Three examples in which molecules crystallize with equal amounts of conformational isomers in the asymmetric unit, despite the covalently linked chiral auxiliary, highlight the limits of the use of the covalent chiral auxiliary approach for asymmetric induction in the solid state.
UR - http://www.scopus.com/inward/record.url?scp=27744530694&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=27744530694&partnerID=8YFLogxK
U2 - 10.1021/cg0501175
DO - 10.1021/cg0501175
M3 - Article
AN - SCOPUS:27744530694
VL - 5
SP - 2348
EP - 2355
JO - Crystal Growth and Design
JF - Crystal Growth and Design
SN - 1528-7483
IS - 6
ER -